Tetrahydrofuran → HCID 68207886, compound

HRID 2175988Notes

Reaction equation

HRID 2175988 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.C1COCC1.[H][H]>[C].[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10636688HCID 10636688, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68207886HCID 68207886, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 50.1 g of methyl 4-[(E)-2-(4-nitrophenyl)vinyl]benzoate, 600 mL of THF, and 200 mL of N,N-dimethylformamide (DMF) was added 10.3 g of 10% palladium carbon (wetted with 55% H2O), followed by stirring for 8 hours at room temperature in a hydrogen atmosphere (1 atm). The inside of the reaction vessel was purged with argon, and then the insoluble material was removed by filtration by using celite. The filtrate was concentrated under reduced pressure, and 1000 mL of water was added to the residue, followed by stirring for 30 minutes at room temperature. The precipitate was collected by filtration, thereby obtaining 44.0 g of methyl 4-[2-(4-aminophenyl)ethyl]benzoate.

Workup

  1. customThe inside of the reaction vessel was purged with argon
  2. customthe insoluble material was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure, and 1000 mL of water
  4. additionwas added to the residue
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c99bb442c6974fc7b55fc03854fd0d62
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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